data_OBN
# 
_chem_comp.id                                    OBN 
_chem_comp.name                                  OUABAIN 
_chem_comp.type                                  NON-POLYMER 
_chem_comp.pdbx_type                             HETAIN 
_chem_comp.formula                               "C29 H44 O12" 
_chem_comp.mon_nstd_parent_comp_id               ? 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    0 
_chem_comp.pdbx_initial_date                     1999-07-08 
_chem_comp.pdbx_modified_date                    2008-10-14 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        584.652 
_chem_comp.one_letter_code                       ? 
_chem_comp.three_letter_code                     OBN 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        ? 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1IBG 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
OBN C1     C1     C 0 1 N N R 6.971  11.837 41.951 0.571  1.426  -1.301 C1     OBN 1  
OBN C2     C2     C 0 1 N N N 5.956  11.967 43.068 1.431  0.219  -1.683 C2     OBN 2  
OBN C3     C3     C 0 1 N N S 5.424  10.621 43.544 0.553  -0.838 -2.354 C3     OBN 3  
OBN C4     C4     C 0 1 N N N 5.039  9.694  42.375 -0.544 -1.280 -1.384 C4     OBN 4  
OBN C5     C5     C 0 1 N N S 5.952  9.664  41.111 -1.403 -0.073 -1.003 C5     OBN 5  
OBN C6     C6     C 0 1 N N N 5.201  9.017  39.930 -2.482 -0.580 -0.045 C6     OBN 6  
OBN C7     C7     C 0 1 N N N 3.869  9.732  39.706 -1.855 -1.136 1.234  C7     OBN 7  
OBN C8     C8     C 0 1 N N R 4.156  11.136 39.215 -0.988 -0.058 1.888  C8     OBN 8  
OBN C9     C9     C 0 1 N N S 4.977  11.961 40.221 0.109  0.398  0.928  C9     OBN 9  
OBN C10    C10    C 0 1 N N R 6.303  11.167 40.690 -0.527 0.986  -0.333 C10    OBN 10 
OBN C11    C11    C 0 1 N N R 5.137  13.402 39.633 0.958  1.473  1.614  C11    OBN 11 
OBN C12    C12    C 0 1 N N N 3.819  14.064 39.249 1.639  0.852  2.831  C12    OBN 12 
OBN C13    C13    C 0 1 N N R 3.065  13.300 38.165 0.601  0.373  3.848  C13    OBN 13 
OBN C14    C14    C 0 1 N N S 2.900  11.825 38.633 -0.430 -0.552 3.180  C14    OBN 14 
OBN C15    C15    C 0 1 N N N 1.705  11.933 39.561 0.384  -1.875 2.988  C15    OBN 15 
OBN C16    C16    C 0 1 N N N 0.873  13.138 39.116 1.228  -1.981 4.279  C16    OBN 16 
OBN C17    C17    C 0 1 N N R 1.648  13.870 38.043 1.347  -0.553 4.844  C17    OBN 17 
OBN C18    C18    C 0 1 N N N 3.859  13.412 36.863 -0.071 1.548  4.561  C18    OBN 18 
OBN C19    C19    C 0 1 N N N 7.371  11.037 39.568 -1.387 2.193  0.045  C19    OBN 19 
OBN C20    C20    C 0 1 N N N 0.968  13.847 36.691 0.701  -0.478 6.204  C20    OBN 20 
OBN C21    C21    C 0 1 N N N 0.909  15.020 35.767 -0.685 -0.953 6.568  C21    OBN 21 
OBN C22    C22    C 0 1 N N N 0.277  12.856 36.079 1.242  0.023  7.311  C22    OBN 22 
OBN C23    C23    C 0 1 N N N -0.301 13.327 34.826 0.289  -0.092 8.418  C23    OBN 23 
OBN "C1'"  "C1'"  C 0 1 N N R 5.748  8.991  45.353 -0.211 -1.366 -4.452 "C1'"  OBN 24 
OBN "C2'"  "C2'"  C 0 1 N N R 6.918  8.356  46.113 -1.123 -0.917 -5.596 "C2'"  OBN 25 
OBN "C3'"  "C3'"  C 0 1 N N R 7.665  9.474  46.885 -0.494 0.296  -6.290 "C3'"  OBN 26 
OBN "C4'"  "C4'"  C 0 1 N N R 6.746  10.100 47.939 0.938  -0.063 -6.699 "C4'"  OBN 27 
OBN "C5'"  "C5'"  C 0 1 N N S 5.356  10.459 47.376 1.694  -0.574 -5.471 "C5'"  OBN 28 
OBN "C6'"  "C6'"  C 0 1 N N N 4.348  10.506 48.518 3.137  -0.902 -5.862 "C6'"  OBN 29 
OBN O1     O1     O 0 1 N N N 8.127  11.092 42.391 -0.023 1.978  -2.477 O1     OBN 30 
OBN O3     O3     O 0 1 N N N 6.290  10.008 44.471 -0.043 -0.287 -3.529 O3     OBN 31 
OBN O5     O5     O 0 1 N N N 7.116  8.812  41.382 -2.020 0.440  -2.186 O5     OBN 32 
OBN O11    O11    O 0 1 N N N 5.871  14.302 40.454 1.945  1.959  0.703  O11    OBN 33 
OBN O14    O14    O 0 1 N N N 2.433  11.051 37.519 -1.506 -0.793 4.088  O14    OBN 34 
OBN O19    O19    O 0 1 N N N 8.233  12.191 39.466 -1.981 2.743  -1.132 O19    OBN 35 
OBN O21    O21    O 0 1 N N N 0.012  14.614 34.691 -0.847 -0.670 7.986  O21    OBN 36 
OBN O23    O23    O 0 1 N N N -1.019 12.769 33.996 0.494  0.279  9.557  O23    OBN 37 
OBN "O2'"  "O2'"  O 0 1 N N N 6.360  7.353  46.995 -1.271 -1.984 -6.536 "O2'"  OBN 38 
OBN "O3'"  "O3'"  O 0 1 N N N 8.921  9.067  47.478 -1.257 0.634  -7.449 "O3'"  OBN 39 
OBN "O4'"  "O4'"  O 0 1 N N N 7.372  11.331 48.314 1.593  1.097  -7.215 "O4'"  OBN 40 
OBN "O5'"  "O5'"  O 0 1 N N N 4.858  9.494  46.394 1.060  -1.749 -4.970 "O5'"  OBN 41 
OBN H1     H1     H 0 1 N N N 7.320  12.855 41.662 1.197  2.180  -0.822 H1     OBN 42 
OBN H21    1H2    H 0 1 N N N 6.372  12.554 43.919 1.886  -0.200 -0.786 H21    OBN 43 
OBN H22A   2H2    H 0 0 N N N 5.120  12.643 42.771 2.213  0.534  -2.374 H22A   OBN 44 
OBN H3     H3     H 0 1 N N N 4.475  10.824 44.093 1.165  -1.698 -2.626 H3     OBN 45 
OBN H41    1H4    H 0 1 N N N 4.923  8.654  42.761 -1.168 -2.032 -1.867 H41    OBN 46 
OBN H42    2H4    H 0 1 N N N 3.994  9.924  42.060 -0.094 -1.703 -0.486 H42    OBN 47 
OBN H61    1H6    H 0 1 N N N 5.821  8.988  39.004 -3.099 -1.348 -0.511 H61    OBN 48 
OBN H62    2H6    H 0 1 N N N 5.068  7.918  40.069 -3.101 0.283  0.199  H62    OBN 49 
OBN H71    1H7    H 0 1 N N N 3.190  9.169  39.023 -1.237 -2.001 0.989  H71    OBN 50 
OBN H72    2H7    H 0 1 N N N 3.218  9.719  40.611 -2.643 -1.437 1.924  H72    OBN 51 
OBN H8     H8     H 0 1 N N N 4.838  11.055 38.337 -1.609 0.814  2.088  H8     OBN 52 
OBN H9     H9     H 0 1 N N N 4.461  12.102 41.199 0.738  -0.450 0.659  H9     OBN 53 
OBN H11    H11    H 0 1 N N N 5.731  13.209 38.709 0.318  2.296  1.933  H11    OBN 54 
OBN H121   1H12   H 0 0 N N N 3.175  14.222 40.146 2.243  0.003  2.509  H121   OBN 55 
OBN H122   2H12   H 0 0 N N N 3.978  15.126 38.950 2.285  1.594  3.299  H122   OBN 56 
OBN H151   1H15   H 0 0 N N N 1.109  10.991 39.610 1.029  -1.801 2.113  H151   OBN 57 
OBN H152   2H15   H 0 0 N N N 1.995  11.981 40.636 -0.288 -2.728 2.899  H152   OBN 58 
OBN H161   1H16   H 0 0 N N N -0.154 12.855 38.789 2.218  -2.374 4.047  H161   OBN 59 
OBN H162   2H16   H 0 0 N N N 0.582  13.799 39.965 0.729  -2.628 5.000  H162   OBN 60 
OBN H17    H17    H 0 1 N N N 1.694  14.976 38.175 2.396  -0.263 4.912  H17    OBN 61 
OBN H181   1H18   H 0 0 N N N 3.307  12.853 36.070 0.661  2.067  5.178  H181   OBN 62 
OBN H182   2H18   H 0 0 N N N 4.069  14.468 36.577 -0.477 2.238  3.821  H182   OBN 63 
OBN H183   3H18   H 0 0 N N N 4.915  13.072 36.972 -0.879 1.176  5.192  H183   OBN 64 
OBN H191   1H19   H 0 0 N N N 7.969  10.105 39.696 -2.170 1.880  0.735  H191   OBN 65 
OBN H192   2H19   H 0 0 N N N 6.890  10.813 38.587 -0.763 2.949  0.523  H192   OBN 66 
OBN H211   1H21   H 0 0 N N N 0.611  15.971 36.265 -1.436 -0.416 5.990  H211   OBN 67 
OBN H212   2H21   H 0 0 N N N 1.908  15.365 35.413 -0.768 -2.025 6.388  H212   OBN 68 
OBN H22    H22    H 0 1 N N N 0.199  11.848 36.520 2.232  0.450  7.383  H22    OBN 69 
OBN "H1'"  "H1'"  H 0 1 N N N 5.171  8.300  44.694 -0.664 -2.214 -3.938 "H1'"  OBN 70 
OBN "H2'"  "H2'"  H 0 1 N N N 7.656  7.866  45.436 -2.100 -0.644 -5.198 "H2'"  OBN 71 
OBN "H3'"  "H3'"  H 0 1 N N N 7.938  10.234 46.116 -0.478 1.142  -5.603 "H3'"  OBN 72 
OBN "H4'"  "H4'"  H 0 1 N N N 6.602  9.376  48.775 0.915  -0.838 -7.465 "H4'"  OBN 73 
OBN "H5'"  "H5'"  H 0 1 N N N 5.470  11.444 46.868 1.694  0.194  -4.699 "H5'"  OBN 74 
OBN "H6'1" "1H6'" H 0 0 N N N 3.342  10.765 48.110 3.677  -1.265 -4.987 "H6'1" OBN 75 
OBN "H6'2" "2H6'" H 0 0 N N N 4.333  9.560  49.108 3.138  -1.672 -6.634 "H6'2" OBN 76 
OBN "H6'3" "3H6'" H 0 0 N N N 4.665  11.196 49.333 3.623  -0.004 -6.243 "H6'3" OBN 77 
OBN HO1    HO1    H 0 1 N N N 8.763  11.010 41.690 0.700  2.208  -3.075 HO1    OBN 78 
OBN HO5    HO5    H 0 1 N N N 7.672  8.793  40.612 -2.516 -0.289 -2.582 HO5    OBN 79 
OBN HOE    HOE    H 0 1 N N N 5.968  15.177 40.097 2.455  2.631  1.175  HOE    OBN 80 
OBN HOF    HOF    H 0 1 N N N 1.661  11.474 37.161 -2.069 -1.466 3.682  HOF    OBN 81 
OBN HON    HON    H 0 1 N N N 8.885  12.111 38.780 -2.513 3.499  -0.850 HON    OBN 82 
OBN "HO2'" "'HO2" H 0 0 N N N 7.085  6.959  47.466 -1.663 -2.726 -6.056 "HO2'" OBN 83 
OBN "HO3'" "'HO3" H 0 0 N N N 9.378  9.752  47.951 -2.151 0.839  -7.145 "HO3'" OBN 84 
OBN "HO4'" "'HO4" H 0 0 N N N 6.802  11.719 48.967 2.489  0.827  -7.459 "HO4'" OBN 85 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
OBN C1    C2     SING N N 1  
OBN C1    C10    SING N N 2  
OBN C1    O1     SING N N 3  
OBN C1    H1     SING N N 4  
OBN C2    C3     SING N N 5  
OBN C2    H21    SING N N 6  
OBN C2    H22A   SING N N 7  
OBN C3    C4     SING N N 8  
OBN C3    O3     SING N N 9  
OBN C3    H3     SING N N 10 
OBN C4    C5     SING N N 11 
OBN C4    H41    SING N N 12 
OBN C4    H42    SING N N 13 
OBN C5    C6     SING N N 14 
OBN C5    C10    SING N N 15 
OBN C5    O5     SING N N 16 
OBN C6    C7     SING N N 17 
OBN C6    H61    SING N N 18 
OBN C6    H62    SING N N 19 
OBN C7    C8     SING N N 20 
OBN C7    H71    SING N N 21 
OBN C7    H72    SING N N 22 
OBN C8    C9     SING N N 23 
OBN C8    C14    SING N N 24 
OBN C8    H8     SING N N 25 
OBN C9    C10    SING N N 26 
OBN C9    C11    SING N N 27 
OBN C9    H9     SING N N 28 
OBN C10   C19    SING N N 29 
OBN C11   C12    SING N N 30 
OBN C11   O11    SING N N 31 
OBN C11   H11    SING N N 32 
OBN C12   C13    SING N N 33 
OBN C12   H121   SING N N 34 
OBN C12   H122   SING N N 35 
OBN C13   C14    SING N N 36 
OBN C13   C17    SING N N 37 
OBN C13   C18    SING N N 38 
OBN C14   C15    SING N N 39 
OBN C14   O14    SING N N 40 
OBN C15   C16    SING N N 41 
OBN C15   H151   SING N N 42 
OBN C15   H152   SING N N 43 
OBN C16   C17    SING N N 44 
OBN C16   H161   SING N N 45 
OBN C16   H162   SING N N 46 
OBN C17   C20    SING N N 47 
OBN C17   H17    SING N N 48 
OBN C18   H181   SING N N 49 
OBN C18   H182   SING N N 50 
OBN C18   H183   SING N N 51 
OBN C19   O19    SING N N 52 
OBN C19   H191   SING N N 53 
OBN C19   H192   SING N N 54 
OBN C20   C21    SING N N 55 
OBN C20   C22    DOUB N N 56 
OBN C21   O21    SING N N 57 
OBN C21   H211   SING N N 58 
OBN C21   H212   SING N N 59 
OBN C22   C23    SING N N 60 
OBN C22   H22    SING N N 61 
OBN C23   O21    SING N N 62 
OBN C23   O23    DOUB N N 63 
OBN "C1'" "C2'"  SING N N 64 
OBN "C1'" O3     SING N N 65 
OBN "C1'" "O5'"  SING N N 66 
OBN "C1'" "H1'"  SING N N 67 
OBN "C2'" "C3'"  SING N N 68 
OBN "C2'" "O2'"  SING N N 69 
OBN "C2'" "H2'"  SING N N 70 
OBN "C3'" "C4'"  SING N N 71 
OBN "C3'" "O3'"  SING N N 72 
OBN "C3'" "H3'"  SING N N 73 
OBN "C4'" "C5'"  SING N N 74 
OBN "C4'" "O4'"  SING N N 75 
OBN "C4'" "H4'"  SING N N 76 
OBN "C5'" "C6'"  SING N N 77 
OBN "C5'" "O5'"  SING N N 78 
OBN "C5'" "H5'"  SING N N 79 
OBN "C6'" "H6'1" SING N N 80 
OBN "C6'" "H6'2" SING N N 81 
OBN "C6'" "H6'3" SING N N 82 
OBN O1    HO1    SING N N 83 
OBN O5    HO5    SING N N 84 
OBN O11   HOE    SING N N 85 
OBN O14   HOF    SING N N 86 
OBN O19   HON    SING N N 87 
OBN "O2'" "HO2'" SING N N 88 
OBN "O3'" "HO3'" SING N N 89 
OBN "O4'" "HO4'" SING N N 90 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
OBN SMILES           ACDLabs              10.04 O=C1OCC(=C1)C4CCC5(O)C3CCC6(O)CC(OC2OC(C(O)C(O)C2O)C)CC(O)C6(CO)C3C(O)CC45C 
OBN InChI            InChI                1.02b 
;InChI=1/C29H44O12/c1-13-22(34)23(35)24(36)25(40-13)41-15-8-19(32)28(12-30)21-17(3-5-27(28,37)9-15)29(38)6-4-16(14-7-20(33)39-11-14)26(29,2)10-18(21)31/h7,13,15-19,21-25,30-32,34-38H,3-6,8-12H2,1-2H3/t13-,15-,16+,17+,18+,19+,21+,22-,23+,24+,25-,26+,27-,28+,29-/m0/s1
;
OBN InChIKey         InChI                1.02b LPMXVESGRSUGHW-HBYQJFLCBJ 
OBN SMILES_CANONICAL CACTVS               3.341 C[C@@H]1O[C@@H](O[C@H]2C[C@@H](O)[C@]3(CO)[C@H]4[C@H](O)C[C@]5(C)[C@H](CC[C@]5(O)[C@@H]4CC[C@]3(O)C2)C6=CC(=O)OC6)[C@H](O)[C@H](O)[C@H]1O 
OBN SMILES           CACTVS               3.341 C[CH]1O[CH](O[CH]2C[CH](O)[C]3(CO)[CH]4[CH](O)C[C]5(C)[CH](CC[C]5(O)[CH]4CC[C]3(O)C2)C6=CC(=O)OC6)[CH](O)[CH](O)[CH]1O 
OBN SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2C[C@H]([C@@]3([C@@H]4[C@@H](CC[C@@]3(C2)O)[C@]5(CC[C@@H]([C@]5(C[C@H]4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O 
OBN SMILES           "OpenEye OEToolkits" 1.5.0 CC1C(C(C(C(O1)OC2CC(C3(C4C(CCC3(C2)O)C5(CCC(C5(CC4O)C)C6=CC(=O)OC6)O)CO)O)O)O)O 
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
OBN "SYSTEMATIC NAME" ACDLabs              10.04 (1alpha,3beta,5beta,11alpha,17alpha)-3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-1,5,11,14,19-pentahydroxycard-20(22)-enolide 
OBN "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 
4-[(1R,3S,5S,8R,9S,10R,11R,13R,14S,17R)-1,5,11,14-tetrahydroxy-10-(hydroxymethyl)-13-methyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-oxan-2-yl]oxy-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-5H-furan-2-one 
# 
